| New phototriggers: extending the p-hydroxyphenacyl pi-pi absorption range. | |
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MedLine Citation:
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PMID: 10841475 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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[equation--see text] Introducing 3-methoxy or 3,5-dimethoxy substituents on the 4-hydroxyphenacyl (pHP) photoremovable protecting group has been explored with two excitatory gamma-amino acids, L-glutamic acid and gamma-amino butyric acid (GABA). These substituents significantly extend the absorption range of the pHP chromophore, e.g., the tail of absorption bands of 2a,b extend above 400 nm, well beyond the absorptions of aromatic amino acids and nucleotides. Irradiation releases the amino acids with rate constants of approximately 10(7) s(-)(1) and appearance efficiencies (Phi(app)) of 0.03-0.04. The photoproducts are formed through the pHP excited triplet and are primarily products of photoreduction and photohydrolysis. 1a,b also rearranged to the phenylacetic acid 3. |
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Authors:
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P G Conrad; R S Givens; J F Weber; K Kandler |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S. |
Journal Detail:
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Title: Organic letters Volume: 2 ISSN: 1523-7060 ISO Abbreviation: Org. Lett. Publication Date: 2000 Jun |
Date Detail:
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Created Date: 2000-07-07 Completed Date: 2000-07-07 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 100890393 Medline TA: Org Lett Country: UNITED STATES |
Other Details:
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Languages: eng Pagination: 1545-7 Citation Subset: IM |
Affiliation:
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Department of Chemistry, University of Kansas, Lawrence 66045, USA. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Acetophenones
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chemistry,
radiation effects Animals Bicuculline / pharmacology Electric Conductivity Electrons Glutamic Acid / chemistry, pharmacology, radiation effects Hippocampus / cytology Ion Channels / drug effects Light Luminescent Measurements Neurons / drug effects, physiology, radiation effects Photolysis* Rats gamma-Aminobutyric Acid / chemistry, pharmacology, radiation effects |
| Chemical | |
Reg. No./Substance:
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0/Acetophenones; 0/Ion Channels; 485-49-4/Bicuculline; 56-12-2/gamma-Aminobutyric Acid; 56-86-0/Glutamic Acid |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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